Diisopropylethylamine → 2-[(6-Chloropyrazolo[4,3-c]pyridin-1-yl)methoxy]ethyl-trimethyl-silane

HRID 57978Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][NH:10][C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.[CH3:20][Si:21]([CH2:24][CH2:25][O:26][CH2:27]Cl)([CH3:23])[CH3:22]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([CH2:27][O:26][CH2:25][CH2:24][Si:21]([CH3:23])([CH3:22])[CH3:20])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of 6-chloro-1H-pyrazolo[4,3-c]pyridine (2.00 g, 13.1 mmol) and DIPEA (3 mL) in DCM (10 mL) was added SEMCl (3 mL). The mixture was stirred at 30° C. for 20 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography using EtOAc/Petroleum Ether (10%˜60%) as eluting solvents to afford 6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridine as colorless oil (3.44 g, 93%). MS (ESI) m/z: 284 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe residue was purified by silica gel chromatography
washas eluting solvents

Sources & evidence

ORD record: ord-068c61179eb841218dd995ff96c532a2
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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